Methyl iodide → 2-(5-Bromo-2-naphthalenyl)propionitrile

Temperature

-78 °C

To a solution of LDA [lithium diisopropylamine prepared from diisopropylamine (1.49 g, 14.8 mmol) and n-BuLi (9.25 mL, 14.8 mmol, 1.6M solution in hexanes)]in THF (80 mL) at -78° C. was added (5-bromo-2-naphthalenyl) acetonitrile (3.80 g, 13.4 mmol) in THF (70 mL) dropwise over 45 minutes. The resulting orange solution was stirred at -78° C. for 10 minutes and MeI (1.90 g, 13.4 mmol) was added in one portion. The reaction mixture was stirred at -78° C. for 1 hour and quenched with saturated NH4Cl (20 mL). The solution was warmed to room temperature and the volatiles removed in vacuo. The residue was diluted with H2O (100 mL) and extracted with Et2O (3×150 mL). The combined organic layers were dried (MgSO)4) and concentrated in vacuo to give the crude product as a yellow oil. This residue was purified by flash chromatography (SiO2) with elution by hexane/CH2Cl2 (2:1), followed by hexane/CH2Cl2 (3:2) to give the title compound as a colorless oil (2.74 g, 79%).

1. stirringThe reaction mixture was stirred at -78° C. for 1 hour
2. customquenched with saturated NH4Cl (20 mL)
3. temperatureThe solution was warmed to room temperature
4. customthe volatiles removed in vacuo
5. additionThe residue was diluted with H2O (100 mL)
6. extractionextracted with Et2O (3×150 mL)
7. concentrationconcentrated in vacuo
8. customto give the crude product as a yellow oil
9. customThis residue was purified by flash chromatography (SiO2) with elution by hexane/CH2Cl2 (2:1)

ORD record

ord-b89cd2da215f488291b5084bd9acfc38

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04895861